| Identification | More | [Name]
3,4-Dimethoxycinnamic acid | [CAS]
2316-26-9 | [Synonyms]
(2E)-3-(3,4-DIMETHOXYPHENYL)ACRYLIC ACID
3-(3,4-DIMETHOXYPHENYL)-2-PROPENOIC ACID
3-(3,4-DIMETHOXY-PHENYL)-ACRYLIC ACID
3',4'-DIMETHOXYCINNAMIC ACID
3,4-DIMETHOXYCINNAMIC ACID
AKOS BB/0042
AKOS BBS-00000090
AURORA 2809
DIMETHYLCAFFEIC ACID
(E)-3-(3,4-DIMETHOXYPHENYL)-2-PROPENOIC ACID
(E)-3-(3,4-DIMETHOXY-PHENYL)-ACRYLIC ACID
OTAVA-BB BB0107620014
RARECHEM BK HC T253
TIMTEC-BB SBB005722
(2E)-3-(3,4-Dimethoxyphenyl)-2-propenoic acid
2-Propenoic acid, 3-(3,4-dimethoxyphenyl)-
3-(3,4-dimethoxyphenyl)propenoicacid
3,4-Dimethoxyphenyl-2-propenoic acid
3,4-Di-O-methylcaffeic acid
Cinnamic acid, 3,4-dimethoxy- | [EINECS(EC#)]
219-025-5 | [Molecular Formula]
C11H12O4 | [MDL Number]
MFCD00004387 | [Molecular Weight]
208.21 | [MOL File]
2316-26-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Slightly yellow to light beige powder | [Melting point ]
181-183 °C(lit.)
| [Boiling point ]
267.4°C (rough estimate) | [density ]
1.0627 (rough estimate) | [refractive index ]
1.4389 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Solubility in hot methanol, very faint turbidity. Soluble in dichloromethane, chloroform. | [form ]
Powder | [pka]
4.53±0.10(Predicted) | [color ]
Slightly yellow to light beige | [BRN ]
1533435 | [InChI]
InChI=1S/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13) | [InChIKey]
HJBWJAPEBGSQPR-GQCTYLIASA-N | [SMILES]
C(O)(=O)C=CC1=CC=C(OC)C(OC)=C1 | [LogP]
2.340 | [CAS DataBase Reference]
2316-26-9(CAS DataBase Reference) | [NIST Chemistry Reference]
3,4-Dimethoxycinnamic acid(2316-26-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29189900 |
| Hazard Information | Back Directory | [Chemical Properties]
Slightly yellow to light beige powder | [Uses]
3,4-Dimethoxycinnamic Acid is a Cinnamic Acid (C442030) derivative,used in the synthesis of amides and esters through coupling reactions involving carboxylic acids and amines and N-methylation of amides and O-methylation of carboxylic acids. | [Definition]
ChEBI: 3,4-dimethoxycinnamic acid is a methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively. It is functionally related to a trans-cinnamic acid. | [Synthesis]
GENERAL METHOD: In a dry reaction vessel, veratraldehyde (500 mg, 1.0 eq.) and malonic acid (981 mg, 2.0 eq.) were dissolved in dimethylformamide (5 mL), followed by the addition of DABCO (105 mg, 0.2 eq.). The reaction mixture was stirred at 100-110°C for 60-90 min. The reaction progress was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was slowly poured into ice water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by recrystallization from a chloroform/hexane solvent mixture to afford 3,4-dimethoxycinnamic acid in good yield. | [storage]
Store at -20°C | [References]
[1] Organic Letters, 2016, vol. 18, # 5, p. 1182 - 1185
[2] Oriental Journal of Chemistry, 2012, vol. 28, # 4, p. 1725 - 1728
[3] Asian Journal of Chemistry, 2017, vol. 29, # 7, p. 1561 - 1564
[4] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 6, p. 1589 - 1594
[5] RSC Advances, 2015, vol. 5, # 34, p. 26596 - 26603 |
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